Anthracene derivative and process of making same.



rin'rrnio satires PATENT OFFICE MAX HENRY ISLER, OF MANNHEIH. GERMANY, ASSIGNOR TO BADISOHE ANILIN & SODA FABRIK, OF LUDWIGSHA'FEN-ON-THE-KHINE. GER- MANY, A CORPORATION.

ANTHRACENE DERIVATIVE AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Patented Sept. 11, 1906.

Application fi ed December 4, 1905. Serial No. 290,275. (Specimens-l To rtZZ whom it may concern:

Be it known that I, MAX HENRY IsLER,

' chemist, a citizen of the Swiss Republic, re-

doanthraquinons which are substituted in.

the ortho position to the amido group I mention 4 chlor 1 amido 2 methylanthraquinon, 4.2 dihalogen- 1 amiddanthraquinon, and also such compounds as contain a halogen and an amido group twice in the position 1.4 relative to one another-for instance,

1 .5-diamido 2 4.6.8 tetrahalogenanthraquinon. The anthraquinon derivatives produced in this way are crystalline and are insoluble in alkalies. They can be converted by sulfonating agentsfor instance, fuming sulfuric acid and boric acid-into sulfo-acids, the salts of which are soluble in water and which dye wool from the acid-bath blue shades of excellent fastness against the action of light, washing, milling, stoving, carbonizing, and steaming.

The following are examples of how my in vention may be performed; but it is not limitcd to these examples: 7 Example 1: Ten (10) kilos of 4-chl0r-1- amido-2-methylanthraquinon are dissolved in one hundred (100) kilos of sulfuric acid of sixty-six (66) degrees Baum in the cold and then treated also in the cold with twelve (12) kilos of nitrating acid, containing about twenty (20) to twenty-one (21) per cent. of I'INO, and seventy-nine (79) to eighty (80) per cent. of H 80 The mass immediately becomes intense red-brown. After stirring for about from one (1) to two (2).hours ten (10) to fifteen kilos of phenol are added, upon which the melt immediately becomes a beautiful-deep blue, which, however, Is not characteristic of the pure end product. Aftor, stirring for about two (2) to three (3) tals.

degrees centigrade.

hours the whole is poured into Water and the precipitate is filtered 0H and washed and dried. hen recrystallized from twenty to thirty parts of napthalene, the substance forms a dark-blue mass of crys- These crystals are insoluble in alkalies, slightly soluble in xylene, the solution being violet and somewhat more readily soluble in nitrobenzene and in anilin, the solutions being blue. The color of the solutions in concentrated sulfuric acid and monohydrate is red-violet. The solution in twenty-three (23) to seventy per cent. oleum is green.

Instead of phenol other phenols or phenol derivativessuch, for instance, as resorcinol, pyrogallol, al haand beta-naphthol, gallic acid, and t e like'or amido compounds-such, for instance, as anilin, alphanaphthylamin, and beta-naphthylamin, 1.5- naphthylenediamin, anthranilic acid, and the like-can be employed, and for the purposes of this invention all these compounds are to be regarded as equivalents, since the phenols and amido compounds do not ap- I parently take part in building up the molecule of the anthracene derivative.

Example II: In order to prepare the sulfocent. of SO and ten (10) kilos of dried boric acid and then heated for about from one (1) to two (2) hours at a temperature of one hundred to one hundred and twenty The melt is oured into water and the coloring matter ltered and washed with weak common-salt solution till it is neutral. It is best used for dyeing in the form of paste. It produces strong blue shades on mordanted and unmordanted wool.

Now what I claim is 1. The process for the production of new anthracene derivatives by treating a 4-halogenl-amidoanthraquinon which is substituted in the 'ortho position to the amido group, with a mixture of nitric acid and sulfuric acid and then with a phenol.

2. The process for the production of new anthraccno derivatives by treating a 4halo gen 1 4 amidoanthraquinon' which is substituted in the ortho position to the amide group, with a mixture of nitric acid and suliuric acid andthen with a phenol .and'after- Ward sulfonating the product obtained.

3. The process for the production of a new anthracene derivative by treating 4-chlor-1- amido-Q-methylanthra uinon with a mixture of nitric acid and su furic' acid and then with phenol.

4. The process for the production of a new anthracene derivative by treating 4-chlor-1- 'amidO-2-met'hylanthra uinon with a mixture of nitric acid and su furic acid and then. with phenol and afterward sulfonating the product obtained. v

5, As newarticles of manufacture thenew anthracene derivatives which can be ob tained by treatinga 4halogen-1-amidoanthraquinon which-1s substituted in the ortho a phenol, which new derivatives are crystal= line and when unsulfonated are insoluble in alkalies, and which in the form of. their sulfoacids dye wool from an acid bath blue shades.

6. As anew article of manufacture the new anthracene derivative whichcan be obtained by treating i-chlor 1-amido-=2-methylanthraquinon with a mixture of nitric acid and sulfuric acid and then with phenol, which new derivative consists of blue 0 stals which when unsulfonated are insolub ein alkalies and which in the form of its sulfo-acid dyesmy hand in the presence-of two subscribing I witnesses.

MAX HENRY ISLER Witnesses:

-J. ALEc. IJLoY'n; Jos. H. LE TE. 

